(2R,3S,6S)-3-allyl-1-benzyl-2-methyl-6-[(trimethylsilyl)ethynyl]-1,2,3,6-tetrahydropyridine | 1092407-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,6S)-3-allyl-1-benzyl-2-methyl-6-[(trimethylsilyl)ethynyl]-1,2,3,6-tetrahydropyridine
• 英文别名: 2-[(2R,3S,6R)-1-benzyl-2-methyl-3-prop-2-enyl-3,6-dihydro-2H-pyridin-6-yl]ethynyl-trimethylsilane
• CAS: 1092407-96-9
• 化学式: C₂₁H₂₉NSi
• 分子量: 323.553
• InChiKey: LNAIOPRWEQSMKO-HLAWJBBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  9-benzyl-8-(iodomethyl)-10-methyl-9-azabicyclo[3.3.2]dec-2-ene 、 magnesium,ethynyl(trimethyl)silane,bromide 在 silver perchlorate 、 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以74%的产率得到(2R,3S,6S)-3-allyl-1-benzyl-2-methyl-6-[(trimethylsilyl)ethynyl]-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Silver Ion-Induced Grob Fragmentation of γ-Amino Iodides: Highly Stereoselective Synthesis of Polysubstituted Piperidines

  摘要：

  A new concerted silver ion-mediated Grob fragmentation process is described in which a 1,2-dihydropyridinium ion is formed and trapped in situ with Grignard reagents in a highly regio- and diastereoselective fashion. Using this methodology, 2,3,6-trisubstituted piperidines were synthesized in good yields and further derivatized to polysubstituted indolizidine.

  DOI：

  10.1021/ol8024605

文献信息

• Silver Ion-Induced Grob Fragmentation of γ-Amino Iodides: Highly Stereoselective Synthesis of Polysubstituted Piperidines
  作者：Guillaume Barbe、Miguel St-Onge、André B. Charette

  DOI：10.1021/ol8024605

  日期：2008.12.4

  A new concerted silver ion-mediated Grob fragmentation process is described in which a 1,2-dihydropyridinium ion is formed and trapped in situ with Grignard reagents in a highly regio- and diastereoselective fashion. Using this methodology, 2,3,6-trisubstituted piperidines were synthesized in good yields and further derivatized to polysubstituted indolizidine.